Synthesis of fully substituted dispirocyclohexanes by organocatalytic [2 + 2 + 2] annulation strategy between 2-arylideneindane-1,3-diones and aldehydes

Hsuan Hao Kuan, Chung Han Chien, Kwunmin Chen

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

An interesting organocatalytic reaction between 2-arylideneindane-1,3- diones and aldehydes has been developed that gives fully substituted cyclohexanes that bear two all-carbon quaternary centers. The dispirocyclohexanes were obtained in reasonable-to-good chemical yields and with high stereoselectivities (>95:5 d.r. and up to 99% ee) using a catalytic amount of commercially available α,α-l-diphenylprolinol trimethylsilyl ether (5 mol %) and DABCO (20 mol %) in DMF at -20 °C. The reaction proceeds through a unique Michael/Michael/aldol reaction that requires 2 equiv of the 2-arylideneindane-1,3-dione.

Original languageEnglish
Pages (from-to)2880-2883
Number of pages4
JournalOrganic Letters
Volume15
Issue number11
DOIs
Publication statusPublished - 2013 Jun 26

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Cyclohexanes
Stereoselectivity
Dione
aldehydes
Aldehydes
Carbon
Michael reaction
synthesis
bears
cyclohexane
ethers
carbon
diphenylprolinol trimethylsilyl ether
triethylenediamine
3-hydroxybutanal

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Synthesis of fully substituted dispirocyclohexanes by organocatalytic [2 + 2 + 2] annulation strategy between 2-arylideneindane-1,3-diones and aldehydes. / Kuan, Hsuan Hao; Chien, Chung Han; Chen, Kwunmin.

In: Organic Letters, Vol. 15, No. 11, 26.06.2013, p. 2880-2883.

Research output: Contribution to journalArticle

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